Novel potential metabolic enzymes inhibitor, photosensitizer and antibacterial agents based on water-soluble phthalocyanine bearing imidazole derivative

Günsel, Armağan; Taslimi, Parham; Atmaca, Göknur Yaşa; Bilgiçli, Ahmet T.; Pişkin, Hasan; Ceylan, Yusuf; Erdoğmuş, Alı; Yaraşir, M. Nilüfer; Gülçın, İlhami

doi:10.1016/j.molstruc.2021.130402

Cited by 39 publications

(31 citation statements)

References 61 publications

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“…CA inhibition leads to a decrease in the modification of urine, urinary alkalis production and eventually metabolic acidosis [26–28,31] . CA inhibitors constitute a class of anti‐glaucoma, diuretic, and antiepileptic drugs to treat diseases such as mouth sores, duodenal and gastric ulcers, osteoporosis and neurological disorders [24] . CAs are inhibited by sulfamates and sulfamides, phenols and polyamines, which are metal complex anions, sulfonamides and derivatives of sulfonamides.…”

Section: Resultsmentioning

confidence: 99%

“…CAs are found in almost all organisms [26] . Mammalian isoforms are classified as α‐CA enzymes [24] . Until now, sixteen different CAs have been described in mammals [23,27,28] …”

Section: Introductionmentioning

confidence: 99%

“…The h CA 7 gene 16q22 was localized on chromosomes. The gene for other cytosolic enzymes ( h CAs I, II, III, and XIII) is localized on chromosomes as 8q22 [24] …”

Section: Introductionmentioning

confidence: 99%

“…Carbonic anhydrases (E.C.4.2.1.1, CA,) constitute a large family of enzymes in Zn‐containing enzymes [23] . The CA family contains eight different species: α‐, β‐, γ‐, δ‐, ζ‐, η‐, θ‐, and t‐CAs [24] . α‐, β‐ and δ‐CA isoenzymes have Zn 2+ ions in their active regions, while γ‐CA isoenzymes probably contain iron ions.…”

Section: Introductionmentioning

confidence: 99%

“…[23] The CA family contains eight different species: α-, β-, γ-, δ-, ζ-, η-, θ-, and t-CAs. [24] α-, βand δ-CA isoenzymes have Zn 2 + ions in their active regions, while γ-CA isoenzymes probably contain iron ions. They also show activity with Zn 2 + and Co 2 + ions ζ-CA isoenzymes use Cd 2 + or Zn 2 + for activity.…”

Section: Introductionmentioning

confidence: 99%

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Inhibition Profiles of Some Symmetric Sulfamides Derived from Phenethylamines on Human Carbonic Anhydrase I, and II Isoenzymes

Topal

Aksu

Gülçın

et al. 2021

Chemistry & Biodiversity

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In this work, the inhibitory effect of some symmetric sulfamides derived from phenethylamines were determined against human carbonic anhydrase (hCA) I, and II isoenzymes, and compared with standard compound acetazolamide. IC50 values were obtained from the Enzyme activity (%)‐[Symmetric sulfamides] graphs. Also, Ki values were calculated from the Lineweaver‐Burk graphs. Some symmetric sulfamides compounds (11–18) demonstrated excellent inhibition effects against hCA I, and II isoenzymes. These compounds demonstrated effective inhibitory profiles with IC50 values in ranging from 21.66–28.88 nM against hCA I, 14.44–30.13 nM against hCA II. Among these compounds, the best Ki value for hCA I (Ki: 8.34±1.60 nM) and hCA II (Ki: 16.40±1.00 nM) is compound number 11. Besides, the IC50 value of acetazolamide used as a standard was determined as hCA I, hCA II 57.75 nM, 49.50 nM, respectively. Moreover, in silico ADME‐Tox study showed that all synthesized compounds (11–18) had good oral bioavailability in light of Jorgensen's rule of three, and of Lipinski's rule of five.

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Section: Resultsmentioning

confidence: 99%

“…CAs are found in almost all organisms [26] . Mammalian isoforms are classified as α‐CA enzymes [24] . Until now, sixteen different CAs have been described in mammals [23,27,28] …”

Section: Introductionmentioning

confidence: 99%

“…The h CA 7 gene 16q22 was localized on chromosomes. The gene for other cytosolic enzymes ( h CAs I, II, III, and XIII) is localized on chromosomes as 8q22 [24] …”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Inhibition Profiles of Some Symmetric Sulfamides Derived from Phenethylamines on Human Carbonic Anhydrase I, and II Isoenzymes

Topal

Aksu

Gülçın

et al. 2021

Chemistry & Biodiversity

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Synthesis and biological evaluation of peripherally tetra‐({6‐[3‐(dimethylamino)phenoxy]hexyl}oxy) substituted water‐soluble phthalocyanines as cholinesterases inhibitors

Bıyıklıoğlu

Baş

Akkaya

et al. 2022

Applied Organom Chemis

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In this paper, we synthesized peripherally tetra‐({6‐[3‐(dimethylamino)phenoxy]hexyl}oxy) substituted water‐soluble metallophthalocyanines (DM‐C6‐CoQ, DM‐C6‐CuQ, DM‐C6‐MnQ) and investigated their in vitro cholinesterases inhibitory properties by using the spectrophotometric method. The results revealed that the compounds inhibited cholinesterases and had remarkable inhibitory effects when compared with galantamine (p < 0.0001). The IC50 values of the compounds ranged from 2.11 ± 0.20 to 16.40 ± 1.25 μM for AChE and BuChE. Also, the inhibitory type and inhibition constant (Ki) of the compounds were evaluated using Lineweaver–Burk and Dixon plots. These plots showed that DM‐C6‐CoQ, DM‐C6‐CuQ, and DM‐C6‐MnQ were mixed inhibitors against AChE and DM‐C6‐MnQ is the strongest binding inhibitor to the enzyme. Also, DM‐C6‐CoQ inhibited BuChE via competitive manner with 10.05 ± 0.55 μM of Ki value. These results demonstrated that the compounds might be effective agents against Alzheimer's disease.

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Quinoline‐fused both non‐peripheral and peripheral Zn^IIand Mg^IIphthalocyanines: Anti‐cholinesterase, anti‐α‐glucosidase, DNA nuclease, antioxidant activities, and in silico studies

Yalazan

Tüzün

Akkaya

et al. 2022

Applied Organom Chemis

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Quinoline-fused Zn II (ZnPc p /ZnPc np ) and Mg II (MgPc p /MgPc np ) phthalocyanines with four 4-methylquinolin-2-ol (1) at non-peripheral or peripheral positions of the phthalocyanine core have been synthesized via cyclotetramerization of phthalonitrile derivatives (CN p /CN np ) in the presence of zinc (II) and magnesium (II) metal ions in this study. After synthesis and characterization processes, anti-cholinesterase, anti-α-glucosidase, DNA nuclease, antioxidant activities, and in silico calculations of both peripheral and non-peripheral Zn II and Mg II phthalocyanines were investigated. The inhibitory effects of metallated phthalocyanines on acetylcholinesterase, butyrylcholinesterase, and α-glucosidase enzymes were tested by spectrophotometric method. Theoretical methods are used to compare both the chemical and biological activities of the studied phthalonitrile derivatives and metallated phthalocyanine compounds.

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Novel potential metabolic enzymes inhibitor, photosensitizer and antibacterial agents based on water-soluble phthalocyanine bearing imidazole derivative

Cited by 39 publications

References 61 publications

Inhibition Profiles of Some Symmetric Sulfamides Derived from Phenethylamines on Human Carbonic Anhydrase I, and II Isoenzymes

Inhibition Profiles of Some Symmetric Sulfamides Derived from Phenethylamines on Human Carbonic Anhydrase I, and II Isoenzymes

Synthesis and biological evaluation of peripherally tetra‐({6‐[3‐(dimethylamino)phenoxy]hexyl}oxy) substituted water‐soluble phthalocyanines as cholinesterases inhibitors

Quinoline‐fused both non‐peripheral and peripheral Zn^IIand Mg^IIphthalocyanines: Anti‐cholinesterase, anti‐α‐glucosidase, DNA nuclease, antioxidant activities, and in silico studies

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Novel potential metabolic enzymes inhibitor, photosensitizer and antibacterial agents based on water-soluble phthalocyanine bearing imidazole derivative

Cited by 39 publications

References 61 publications

Inhibition Profiles of Some Symmetric Sulfamides Derived from Phenethylamines on Human Carbonic Anhydrase I, and II Isoenzymes

Inhibition Profiles of Some Symmetric Sulfamides Derived from Phenethylamines on Human Carbonic Anhydrase I, and II Isoenzymes

Synthesis and biological evaluation of peripherally tetra‐({6‐[3‐(dimethylamino)phenoxy]hexyl}oxy) substituted water‐soluble phthalocyanines as cholinesterases inhibitors

Quinoline‐fused both non‐peripheral and peripheral ZnIIand MgIIphthalocyanines: Anti‐cholinesterase, anti‐α‐glucosidase, DNA nuclease, antioxidant activities, and in silico studies

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Quinoline‐fused both non‐peripheral and peripheral Zn^IIand Mg^IIphthalocyanines: Anti‐cholinesterase, anti‐α‐glucosidase, DNA nuclease, antioxidant activities, and in silico studies